Synthesis of Calix[4]resorcinarenes Bearing Thioether Functionality at the Extraannular Positions

Osamu Morikawa; Makoto Miyashiro; Hiroshi Yamaguchi; Kazuhiro Kobayashi; Hisatoshi Konishi

doi:10.1080/10610279908048717

Synthesis of Calix[4]resorcinarenes Bearing Thioether Functionality at the Extraannular Positions

Osamu Morikawa, Makoto Miyashiro, Hiroshi Yamaguchi, Kazuhiro Kobayashi, Hisatoshi Konishi

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

The reactions of calix[4]resorcinarene 1 with thiols and formaldehyde in the presence of triethylamine gave tetrakis(thiomethylated)calix[4]resorcinarenes 3 in good yield. 1 HNMR characterization shows that in CDCl₃ solution these compounds exist in a cone conformation. The presence of a circular hydrogen bonding network consisting of two types of intramolecular hydrogen bondings, OH⋯S and OH⋯OH, is indicated based on IR spectroscopy.

Original language	English
Pages (from-to)	67-72
Number of pages	6
Journal	Supramolecular Chemistry
Volume	11
Issue number	1
DOIs	https://doi.org/10.1080/10610279908048717
Publication status	Published - 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry

Access to Document

10.1080/10610279908048717

Cite this

@article{8d4226bd7b194efd914d385abada8eac,

title = "Synthesis of Calix[4]resorcinarenes Bearing Thioether Functionality at the Extraannular Positions",

abstract = "The reactions of calix[4]resorcinarene 1 with thiols and formaldehyde in the presence of triethylamine gave tetrakis(thiomethylated)calix[4]resorcinarenes 3 in good yield. 1 HNMR characterization shows that in CDCl3 solution these compounds exist in a cone conformation. The presence of a circular hydrogen bonding network consisting of two types of intramolecular hydrogen bondings, OH⋯S and OH⋯OH, is indicated based on IR spectroscopy.",

author = "Osamu Morikawa and Makoto Miyashiro and Hiroshi Yamaguchi and Kazuhiro Kobayashi and Hisatoshi Konishi",

year = "1999",

doi = "10.1080/10610279908048717",

language = "English",

volume = "11",

pages = "67--72",

journal = "Supramolecular Chemistry",

issn = "1061-0278",

publisher = "Taylor and Francis Ltd.",

number = "1",

}

TY - JOUR

T1 - Synthesis of Calix[4]resorcinarenes Bearing Thioether Functionality at the Extraannular Positions

AU - Morikawa, Osamu

AU - Miyashiro, Makoto

AU - Yamaguchi, Hiroshi

AU - Kobayashi, Kazuhiro

AU - Konishi, Hisatoshi

PY - 1999

Y1 - 1999

N2 - The reactions of calix[4]resorcinarene 1 with thiols and formaldehyde in the presence of triethylamine gave tetrakis(thiomethylated)calix[4]resorcinarenes 3 in good yield. 1 HNMR characterization shows that in CDCl3 solution these compounds exist in a cone conformation. The presence of a circular hydrogen bonding network consisting of two types of intramolecular hydrogen bondings, OH⋯S and OH⋯OH, is indicated based on IR spectroscopy.

AB - The reactions of calix[4]resorcinarene 1 with thiols and formaldehyde in the presence of triethylamine gave tetrakis(thiomethylated)calix[4]resorcinarenes 3 in good yield. 1 HNMR characterization shows that in CDCl3 solution these compounds exist in a cone conformation. The presence of a circular hydrogen bonding network consisting of two types of intramolecular hydrogen bondings, OH⋯S and OH⋯OH, is indicated based on IR spectroscopy.

UR - http://www.scopus.com/inward/record.url?scp=0033262796&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033262796&partnerID=8YFLogxK

U2 - 10.1080/10610279908048717

DO - 10.1080/10610279908048717

M3 - Article

AN - SCOPUS:0033262796

SN - 1061-0278

VL - 11

SP - 67

EP - 72

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

IS - 1

ER -

Synthesis of Calix[4]resorcinarenes Bearing Thioether Functionality at the Extraannular Positions

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this